Field of the Invention PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =NH(CH.sub.2).sub.2 --N (C.sub.2 H.sub.5).sub.2 2HCl; R.sub.6 =4-Cl PA0 M.P. 184.degree.-185.degree. C. PA0 H-NMR (D.sub.2 O), .delta. (p.p.m.): 1.25 (t, 2xCH.sub.3) 3.15 (q, 2xCH.sub.3) 3.6 (m, 2xCH.sub.2) 5.8 (s, CH) 6.7-7.6 (m, 2xC.sub.6 H.sub.4, CH) PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H ##STR5## R.sub.6 =4-Cl M.P.=194.degree.-196.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H ##STR6## R.sub.6 =4-Cl M.P. 116.degree.-117.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H ##STR7## R.sub.6 =4-CH.sub.3 M.P. 101.degree.-102.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H ##STR8## R.sub.6 =4-CH.sub.3 M.P. 187.degree.-189.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H ##STR9## R.sub.6 =4-CH.sub.3 M.P. 218.degree.-220.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H ##STR10## R.sub.6 =4-Cl M.P. 176.degree.-178.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =R.sub.6 =H ##STR11## M.P. 77.degree.-79.degree. C. H-NMR (CCl.sub.4); .delta. (p.p.m.): 1.4 (m, 3xCH.sub.2) 2.4 (m, 2xCH.sub.2) 4.5 (s, CH) 6.5 (s, CH) 7-7.6 (m, C.sub.6 H.sub.4, C.sub.6 H.sub.5) PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =R.sub.6 =H ##STR12## M.P. 179.degree.-180.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =R.sub.6 =H ##STR13## M.P. 97.degree.-99.degree. C. H-NMR (CDCl.sub.3); .delta. (p.p.m.): 2.3 (s, CH.sub.3) 2.4-2.6 (m, 4xCH.sub.2) 4.55 (s, CH) 6.6 (s, CH) 7-7.6 (m, C.sub.6 H.sub.4, C.sub.6 H.sub.5) PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H ##STR14## R.sub.6 =4-Cl M.P. 170.degree.-172.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H ##STR15## R.sub.6 =4-Cl M.P. 164.degree.-166.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =R.sub.6 =H ##STR16## M.P. 183.degree.-185.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =R.sub.6 =H ##STR17## M.P. 184.degree.-186.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =NH.sub.2 HCl; R.sub.6 =4-Cl PA0 M.P. 225.degree.-229.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H ##STR18## R.sub.6 =4-Cl M.P. 170.degree.-172.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =R.sub.6 =H; R.sub.5 =NH(CH.sub.2).sub.2 N(C.sub.2 H.sub.5).sub.2.HCl PA0 M.P. 190.degree.-192.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =NH(CH.sub.2).sub.2 N(CH.sub.3).sub.2 HCl; R.sub.6 =4-Cl PA0 M.P. 180.degree.-182.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =NH(CH.sub.2).sub.3 N(CH.sub.3).sub.2.HCl; R.sub.6 =4-Cl PA0 M.P. 139.degree.-141.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =R.sub.6 =H; R.sub.5 =NH(CH.sub.2).sub.2 N(CH.sub.3).sub.2.HCl PA0 M.P. 189.degree.-191.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =NH(CH.sub.2).sub.2 N(CH.sub.3)(C.sub.2 H.sub.5).sub.2 Br; R.sub.6 =4-Cl PA0 M.P. 140.degree.-142.degree. C. PA0 Form. I: R.sub.1 =5-Br R.sub.2 =R.sub.3 =R.sub.4 =R.sub.6 =H; R.sub.5 =NH(CH.sub.2).sub.2 N(C.sub.2 H.sub.5).sub.2.HCl PA0 M.P. 175.degree.-177.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =NH(CH.sub.2).sub.2 N(C.sub.2 H.sub.5).sub.2.HCl; R.sub.6 =4-CH.sub.3 PA0 M.P. 200.degree.-202.degree. C. PA0 H-NMR (D.sub.2 O); .delta. (p.p.m.): 1.15 (t, 2xCH.sub.3) 2.0 (s, CH.sub.3) 3.1 (q, 2xCH.sub.2) 3.4 (m, 2xCH.sub.2) 5.6 (s, CH) 6.7 (s, CH) 6.8-7.4 (m, 2xC.sub.6 H.sub.4) PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =R.sub.6 =H ##STR19## M.P. 174.degree.-175.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =OCONHCH.sub.3 ; R.sub.6 =4-Cl PA0 M.P. 98.degree.-99.degree. C. PA0 Form. I: R.sub.1 and R.sub.2 =C.sub.4 H.sub.4 ; R.sub.3 =R.sub.4 =H R.sub.5 =OH; R.sub.6 =4-Cl PA0 M.P. 101.degree.-103.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =OH; R.sub.6 =4-CH.sub.3 PA0 M.P. 50.degree.-52.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =OH; R.sub.6 =4-F PA0 M.P. 47.degree.-49.degree. C. PA0 H-NMR (CCl.sub.4); .delta. (p.p.m.): 3.75 (s, OH) 5.65 (s, CH) 6.3 (s, CH) 6.7-7.5 (m, 2xC.sub.6 H.sub.4) PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =H; R.sub.4 =CH.sub.3 ; R.sub.5 =OH; R.sub.6 =4-Cl PA0 M.P. 63.degree.-66.degree. C. PA0 H-NMR (CDCl.sub.3); .delta. (p.p.m.): 1.9 (s, CH.sub.3) 2.85 (s, OH) 6.55 (s, CH) 7.0-7.6 (m, 2xC.sub.6 H.sub.4) PA0 Form. I: R.sub.1 =R.sub.3 =R.sub.4 =H; R.sub.2 =5-Br; R.sub.5 =OH; R.sub.6 =4-Cl PA0 M.P. 82.degree.-83.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =OH; R.sub.6 =2-CH.sub.3 PA0 M.P. 72.degree.-75.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.4 =H; R.sub.3 =CH.sub.3 ; R.sub.5 =OH; R.sub.6 =4-Cl PA0 M.P. 89.degree.-91.degree. C. PA0 H-NMR (CDCl.sub.3); .delta. (p.p.m.): 2.2 (s, CH.sub.3) 3.1 (d, OH) 6.0 (d, CH) 7.2-7.6 (m, 2xC.sub.6 H.sub.4) PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =H; R.sub.4 =CH.sub.2 -C.sub.6 H.sub.5 ; R.sub.5 =OH; R.sub.6 =4-Cl PA0 M.P. 129.degree.-131.degree. C. PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 OH; R.sub.6 =4-C.sub.6 H.sub.5 PA0 M.P. 123.degree.-125.degree. C. PA0 Form. I: R.sub.1 =4-OCH.sub.3 ; R.sub.2 =6-OCH.sub.3 ; R.sub.3 =R.sub.4 =H; R.sub.5 =OH; R.sub.6 =4-Cl PA0 M.P. 82.degree.-83.degree. C. PA0 H-NMR (CDCL.sub.3); .delta. (p.p.m.): 2.9 (d, OH) 3.8 (s, CH.sub.3) 3.85 (s, CH.sub.3) 5.85 (d, CH) 6.3-7.4 (m, C.sub.6 H.sub.4, C.sub.6 H.sub.2, CH) PA0 Form. I: R.sub.1 =5-Br; R.sub.2 =R.sub.3 =R.sub.4 =R.sub.6 =H; R.sub.5 =OH PA0 M.P. 56.degree.-58.degree. C. PA0 Form. I: R.sub.1 =7-OC.sub.2 H.sub.5 ; R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =OH; R.sub.6 =4-Cl PA0 H-NMR (CDCl.sub.3): .delta. (p.p.m.) 1.4 (t, CH.sub.3) 3.5 (s, OH) 4.1 (q, CH.sub.2) 5.85 (s, CH) 6.4 (s, CH) 6.6-7.4 (m, C.sub.6 H.sub.4, C.sub.6 H.sub.3) PA0 Form. I. R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 H; R.sub.5 =OH; R.sub.6 =4NO.sub.2 PA0 M.P. 108.degree.-110.degree. C. PA0 Form: I. R.sub.1 =7-OC.sub.2 H.sub.5 ; R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =OH; R.sub.6 =4NO.sub.2 PA0 M.P. 127.degree.-128.degree. C. PA0 Form. I. R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =NH(CH.sub.2).sub.2 N(CH.sub.3).sub.2.2HCl; R.sub.6 =4-F PA0 M.P. 179.degree.-181.degree. C. PA0 H-NMR (D.sub.2 O); .delta. (p.p.m.): 3.2 (s, 2xCH.sub.3) 3.7-3.9 (m, 2xCH.sub.2) 6.05 (s, CH) 7.0 (s, CH) 7.1-8.0 (m, 2xC.sub.6 H.sub.4) PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =NHCH(CH.sub.3).sub.2.HCl; R.sub.6 =4-Cl PA0 M.P. 219.degree.-220.degree. C. PA0 Form. I.: R.sub.1 =7-OCH.sub.3 ; R.sub.2 =R.sub.3 =H; R.sub.4 =CH.sub.2 C.sub.6 H.sub.5 ; R.sub.5 =OH; R.sub.6 =4-Cl PA0 M.P. 130.degree.-132.degree. C. PA0 I.R. (nujol) .nu. (cm.sup.-1): 3540 (OH) PA0 H-NMR (CDCl.sub.3); .delta. (p.p.m.): 2.8 (s, OH) 2.6 (q, CH.sub.2) 4.0 (s, CH.sub.3) 6.5 (s, CH) 6.6-7.8 (m, C.sub.6 H.sub.5, C.sub.6 H.sub.3) PA0 Form. I.: R.sub.1 =7-OCH.sub.3 ; R.sub.2 =R.sub.3 =H; R.sub.4 =CH.sub.3 ; R.sub.5 =OH; R.sub.6 =4-Cl PA0 M.P. 76.degree.-78.degree. C. PA0 Form. I.: R.sub.1 and R.sub.2 =C.sub.4 H.sub.4 ; R.sub.3 =R.sub.4 =R.sub.6 =H; R.sub.5 =OH PA0 M.P. 97.degree.-99.degree. C. PA0 Form. I: R.sub.1 =7-OCH.sub.3 ; R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =OH; R.sub.6 =4-Cl PA0 Form. II.: R.sub.1 =7-OC.sub.2 H.sub.5 ; R.sub.2 =R.sub.3 =H; R.sub.6 =4-C.sub.6 H.sub.5 PA0 M.P. 85.degree.-86.degree. C. PA0 I.R. (nujol) .nu. (cm.sup.-1): 1640 (C.dbd.O) PA0 H-NMR (CDCl.sub.3); .delta. (p.p.m.): 1.5 (t, CH.sub.3) 4.30 (q, CH.sub.2) 6.8-8.2 (m, C.sub.6 H.sub.5, C.sub.6 H.sub.4, C.sub.6 H.sub.3, CH) PA0 Form. II: R.sub.1 =7-OC.sub.2 H.sub.5 ; R.sub.2 =R.sub.3 =H; R.sub.6 =4-Cl PA0 M.P. 108.degree.-110.degree. C. PA0 H-NMR (CDCl.sub.3); .delta. (p.p.m.): 1.5 (t, CH.sub.3) 4.25 (q, CH.sub.2) 6.8-8.2 (m, C.sub.6 H.sub.4, C.sub.6 H.sub.3, CH) PA0 Form. II: R.sub.1 =7-OCH.sub.3 R.sub.2 =R.sub.3 =H R.sub.6 =4-Cl PA0 M.P. 77.degree.-78.degree. C. PA0 I.R. (nujol) .nu. (cm.sup.-1): 1635 (C.dbd.O) PA0 H-NMR (CDCl.sub.3); .delta. (p.p.m.): 4.0 (s, CH.sub.3) 6.9-8.2 (m, C.sub.6 H.sub.4, C.sub.6 H.sub.3) PA0 Form. II: R.sub.1 =7-OC.sub.2 H.sub.5 ; R.sub.2 =R.sub.3 =H; R.sub.6 =4-NO.sub.2 PA0 M.P. 164.degree.-166.degree. C. PA0 I.R. (nujol) .nu. (cm.sup.-1): 1660 (C.dbd.O) PA0 H-NMR (D M SO); .delta. (p.p.m.): 1.7 (t, CH.sub.3) 4.5 (q, CH.sub.2) 7.4-8.8 (m, C.sub.6 H.sub.4, C.sub.6 H.sub.3) PA0 Form. II: R.sub.1 =R.sub.2 =R.sub.3 =H; R.sub.6 =4-C.sub.6 H.sub.5 PA0 M.P. 153.degree.-155.degree. C. PA0 I.R. (nujol) .nu. (cm.sup.-1): 1640 (C.dbd.O) PA0 Form. II: R.sub.1 =R.sub.2 =R.sub.3 =H R.sub.6 =2-OCH.sub.3 PA0 M.P. 78.degree.-80.degree. C. PA0 I.R. (nujol) .nu. (cm.sup.-1): 1645 (C.dbd.O) PA0 H-NMR (CDCl.sub.3); .delta. (p.p.m.): 3.75 (s, CH.sub.3) 6.8-7.7 (m, 2xC.sub.6 H.sub.4) PA0 Form. II: R.sub.1 =4-OCH.sub.3 R.sub.2 =6-OCH.sub.3 R.sub.3 =H R.sub.6 =4-Cl PA0 M.P. 161.degree.-163.degree. C. PA0 Form. I: R.sub.1 =5-Br R.sub.2 =R.sub.3 =R.sub.4 =R.sub.6 =H R.sub.5 =NH(CH.sub.2).sub.2 N(CH.sub.3).sub.2.2HCl PA0 M.P. 181.degree.-183.degree. C. PA0 H-NMR (D.sub.2 O); .delta. (p.p.m.): 3.3 (s, 2xCH.sub.3) 3.9-4.0 (m, 2xCH.sub.2) 6.0 (s, CH) 7.0 (s, CH) 7.05-8.0 (m, C.sub.6 H.sub.5, C.sub.6 H.sub.3) PA0 Form. II: R.sub.1 =5-OCH.sub.3 R.sub.2 =R.sub.3 =H R.sub.6 =4-Cl PA0 M.P. 140.degree.-142.degree. C. PA0 I.R. (nujol) .nu. (cm.sup.-1): 1640 (C.dbd.O) PA0 H-NMR (CDCl.sub.3): .delta. (p.p.m.): 3.9 (s, CH.sub.3) 7.0-8.2 (m, C.sub.6 H.sub.4, C.sub.6 H.sub.3, CH) PA0 Form. II: R.sub.1 =6-OCH.sub.3 ; R.sub.2 =R.sub.3 =H; R.sub.6 =4-Cl PA0 M.P. 186.degree.-187.degree. C. PA0 I.R. (nujol) .nu. (cm.sup.-1): 1630 (C.dbd.O) PA0 Form. I: R.sub.1 =7-OC.sub.2 H.sub.5 ; R.sub.2 =R.sub.3 =H; R.sub.4 =CH.sub.2 -C.sub.6 H.sub.5 ; R.sub.5 =OH; R.sub.6 =4-Cl PA0 M.P. 112.degree.-114.degree. C. PA0 I.R. (nujol) .nu. (cm.sup.-1): 1620 (C.dbd.O) PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H; R.sub.5 =N(CH.sub.3)-(CH.sub.2).sub.2 -N(CH.sub.3).sub.2.2HCl.0.5 H.sub.2 O PA0 M.P. 165.degree.-167.degree. C. PA0 H-NMR (D.sub.2 O); .delta. (p.p.m.): 3.2 (s, CH.sub.3) 3.35 (s, 2xCH.sub.3) 6.2 (s, CH) 7.2-8.1 (m, 2xC.sub.6 H.sub.4, CH) PA0 Form. I: R.sub.1 =R.sub.2 =R.sub.3 =R.sub.4 =H; ##STR20## R.sub.6 =4-Cl M.P. 135.degree.-136.degree. C. PA0 Form. II: R.sub.1 and R.sub.2 =C.sub.4 H.sub.4 ; R.sub.3 =R.sub.6 =H PA0 M.P. 101.degree.-102.degree. C. PA0 I.R. (nujol) .nu. (cm.sup.-1): 1630 (C.dbd.O) PA0 Form. II: R.sub.1 and R.sub.2 =C.sub.4 H.sub.4 R.sub.3 =H R.sub.6 =4-Cl PA0 M.P. 156.degree.-158.degree. C. PA0 I.R. (nujol) .nu. (cm.sup.-1): 1630 (C.dbd.O) R.sub.6 =4-Cl
This invention relates to new pharmacologically active 2-substituted benzofuran derivatives, and methods for their preparation.
Certain benzofuran derivatives have been described in Italian Pat. No. 4139/63 and in Boll.Chim.Farm.109,48(1970).